Dimethylamine → (S)-2-(4-(1-(3-fluorobenzyl)-1H-indazol-5-ylamino)quinazolin-5-yloxy)-N,N-dimethylpropanamide

HRID 1162238Notes

Reaction equation

HRID 1162238 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]=4[O:26][C@@H:27]([CH3:32])[C:28]([O:30]C)=O)[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1.[CH3:36][NH:37][CH3:38]>>[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]=4[O:26][C@@H:27]([CH3:32])[C:28]([N:37]([CH3:38])[CH3:36])=[O:30])[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 86627836methyl (2S)-2-[(4-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate

Product 1

HCID 16117483(S)-2-(4-(1-(3-fluorobenzyl)-1H-indazol-5-ylamino)quinazolin-5-yloxy)-N,N-dimethylpropanamideYield 56%

Procedure

A solution of methyl (2S)-2-[(4-{[1-(3-fluorobenzyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate (200 mg, 0.42 mmol) in 6N methanolic dimethylamine (10 ml) was stirred for 18 hours. After evaporation of the solvents, the residue was purified by chromatography on silica gel (eluant: 2% methanol in dichloromethane) to give the title compound as a beige solid (115 mg, 56%); NMR Spectrum 1.59 (d, 3H), 2.94 (s, 3H), 3.15 (s, 3H), 5.71 (s, 2H), 5.86 (q, 1H), 7.07 (m, 3H), 7.30 (d, 1H), 7.36 (m, 2H), 7.74 (m, 2H), 7.84 (m, 1H), 8.17 (s, 1H), 8.51 (s, 1H), 8.55 (s, 1H); Mass spectrum 485.

Workup

  1. customAfter evaporation of the solvents
  2. customthe residue was purified by chromatography on silica gel (eluant: 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-6433feb8c3ed49508e753a17ee60815b
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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